Silicone-based antimicrobial composition

Abstract

The present invention relates to a composition, comprising: at least one non-crosslinked silicone, and at least one antimicrobial agent dispersed within said silicone, said antimicrobial agent being selected from the group consisting of polymers of ionenes, and of ionic liquids with a molecular mass of less than 1,400 g/mol.

1 . A composition, comprising:
 at least one non-crosslinked silicone, and   at least one antimicrobial agent dispersed within said silicone, said antimicrobial agent being selected from the group consisting of polymers of ionenes, and of ionic liquids with a molecular mass of less than 1,400 g/mol.   
     
     
         2 . The composition according to  claim 1 , wherein the non-crosslinked silicone is a poly(dimethylsiloxane). 
     
     
         3 . The composition according to  claim 1 , wherein the mass proportion of antimicrobial agent is from 1% to 10% based on the total mass of the composition. 
     
     
         4 . The composition according to  claim 1 , wherein the antimicrobial agent is a poly(polymethylene) guanidine salt, comprising n recurrent units of formula (I-1): 
       
         
           
           
               
               
           
         
         wherein:
 p is comprised from 2 to 12, 
 n is comprised from 4 to 140, 
 HA is selected from the group consisting of (CF 3 SO 2 ) 2 NH, HPF 6  and R—SO 3 H, 
 R is selected from the group consisting of C 4 -C 12  perfluoroalkyl groups and C 4 -C 10  aryl groups substituted with at least one group R′, and 
 
         R′ is selected from the group consisting of H; C 1 -C 18  alkyl groups; —NH—CO—R″ groups wherein R″ is a C 1 -C 17  alkyl group or a C 4 -C 10  aryl group; and groups —NH—SO 2 —C 6 H 4 —R′″ wherein R′″ is a hydrogen atom or a C 1 -C 6  alkyl group. 
       
     
     
         5 . The composition according to  claim 4 , wherein n=6 and HA represents dodecylbenzenesulfonic acid of formula: 
       
         
           
           
               
               
           
         
       
     
     
         6 . The composition according to  claim 1 , wherein the antimicrobial agent is a salt of poly(polymethylene)imidazolium, comprising n′ recurrent units of formula (I-2): 
       
         
           
           
               
               
           
         
         wherein:
 m is comprised from 6 to 12, 
 n′ is comprised from 10 to 100, and 
 A −  is selected from the group consisting of BF 4   − , PF 6   −  and (CF 3 SO 2 ) 2 N − . 
 
       
     
     
         7 . The composition according to  claim 1 , wherein the antimicrobial agent is an 1,3-dialkylimidazolium ionic liquid fitting the formula (II-1): 
       
         
           
           
               
               
           
         
         wherein:
 A −  is selected from the group consisting of BF 4   − , PF 6   −  and (CF 3 SO 2 ) 2 N − , 
 R 1  is a C 1 -C 16  alkyl group or a C 5 -C 16  alkylaryl group, and 
 R 2  is selected from the group consisting of C 4 -C 16  alkyl groups, C 5 -C 16  alkylaryl groups and groups of formula (II-1′): 
 
       
       
         
           
           
               
               
           
         
         
           wherein n″ is comprised from 6 to 12, R 1  and A −  are as defined above. 
         
       
     
     
         8 . The composition according to  claim 7 , wherein the antimicrobial agent is 1-octyl-3-methylimidazolinium tetrafluoroborate or 1-dodecyl-3-methylimidazolinium tetrafluoroborate. 
     
     
         9 . The composition according to  claim 1 , wherein the antimicrobial agent is a guanidinium ionic liquid fitting the formula (II-2): 
       
         
           
           
               
               
           
         
         wherein:
 R 1  represents a hydrogen atom or a C 12 -C 16  alkyl group, 
 R 2  represents a C 4 -C 16  alkyl group, 
 HA is selected from the group consisting of (CF 3 SO 2 ) 2 NH, HPF 6  and R—SO 3 H, 
 R is selected from the group consisting of C 4 - 12  perfluoroalkyl groups and C 4 -C 10  aryl groups substituted with a group R′, and 
 R′ is selected from the group consisting of H; C 1 -C 18  alkyl groups; —NH—CO—R″ groups wherein R″ is a C 1 -C 17  alkyl group or a C 4 -C 10  aryl group; and groups —NH—SO 2 —C 6 H 4 —R′″ wherein R′″ is a hydrogen atom or a C 1 -C 6  alkyl group. 
 
       
     
     
         10 . The composition according to  claim 1 , wherein the antimicrobial agent is a phosphonium ionic liquid fitting the formula (II-3): 
       
         
           
           
               
               
           
         
         wherein:
 R is a C 4 -C 12  alkyl group, 
 R′ is selected from the group consisting of C 2 -C 16  alkyl groups, C 5 -C 16  alkylaryl groups, and groups of formula (II-3′): 
 
       
       
         
           
           
               
               
           
         
         
           wherein n′″ is comprised from 6 to 12, R being as defined above, and 
           A −  is selected from the group consisting of BF 4   − , (CF 3 SO 2 ) 2 N − , PF 6   − , P(O)(OR 1 ) 2 O −  and R 2 —SO 3   − , 
           R 1  is an alkyl group C 4 -C 8 , 
           R 2  is selected from the group consisting of C 4 -C 12  perfluoroalkyl groups, C 8 -C 18  alkyl groups, and C 4 -C 10  aryl groups substituted with a group R 3 , and 
           R 3  is selected from the group consisting of H; C 1 -C 18  alkyl groups; —NH—CO—R 4  groups wherein R 4  is a C 1 -C 17  alkyl group or a C 4 -C 10  aryl group; and groups —NH—SO 2 —C 6 H 4 —R 5  wherein R 5  is a hydrogen atom or a C 1 -C 6  alkyl group. 
         
       
     
     
         11 . An antimicrobial article, comprising:
 at least one crosslinked silicone, and   at least one antimicrobial agent dispersed within said crosslinked silicone, said antimicrobial agent being as defined in  claim 1 .   
     
     
         12 . The antimicrobial article according to  claim 11 , having a desalting rate of the antimicrobial agent of less than 5% per year.